Holiday Playlist No. 2: Sentimental Stuffing

The ultimate sentimental holiday playlist: 100 holiday songs for those who like it dreamy and sad (5 hrs)

Frank Sinatra in a Christmas Tree

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Holiday gifts for the musically curious

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Holiday Playlist No. 2: Ultimate Sentimental Holiday Playlist (5 hrs)

Here’s the second installment of my holiday playlist trilogy

I’ve been building and fine-tuning this playlist for years, and the 2025 version is especially dreamy and sad — which is exactly how I like my holiday music. It’s hard to beat this stuff.

Fats Waller

This is the music that plays in our house every evening for the entire month of December. Everyone hears Holiday music differently, but to my ear this is 100% great stuff. I hear no schmaltz. No cheese. Just pure sentimental holiday goodness.

Peggy Lee

Mildred Bailey

Tidal, Spotify, Apple Music and…YouTube Music playlists below.

YES!! I added YouTube Music!

Happy Holidays!

-walt